Curator’s statement
Away from the bustling tourist hubs, these destinations offer a glimpse into the authentic heart of Italy. From the vineyard-clad hills of Tuscany to the coastlines of Puglia, each town beckons with its own unique allure and rich history. Join us as we wander cobblestone streets, explore ancient cave dwellings and savor the flavors of regional cuisine. Whether you're drawn to medieval architecture, breathtaking landscapes or cultural immersion, these off-the-beaten-path gems promise an unforgettable adventure filled with discovery and enchantment.
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Where to stay in Italy
La Corte Antica, Pienza
A charming boutique hotel nestled in the heart of Pienza, offering a timeless escape amidst Tuscany's historic beauty.
Palazzo Calò
An elegant retreat in the heart of Lecce, blending historic charm with modern luxury in a beautifully restored palace setting.
Hotel Fortuna
A tranquil oasis in the heart of Perugia, combining modern comfort with historic charm in a picturesque Italian setting.
Unlock perks by contacting Marc to book your trip.
Things to do in Italy
Embark on a journey through Italy's lesser-known treasures, where hidden gems and charming towns await those willing to stray from the beaten path. From the sun-drenched hills of Tuscany to the rugged coastline of Puglia, each destination offers a unique glimpse into Italy's rich cultural tapestry. Prepare to be enchanted as we uncover the secrets of these off-the-beaten-path gems.
Montepulciano
Our adventure begins in Montepulciano, a picturesque hilltop town nestled in the heart of Tuscany. Here, cobblestone streets wind their way through Renaissance palaces and ancient churches, offering a glimpse into the region's storied past. Explore the town's hidden corners and panoramic viewpoints, where vineyards stretch as far as the eye can see. Don't miss the chance to sample the local Vino Nobile wine, renowned for its rich flavors and velvety texture.
Matera
Next, we journey to Matera, a city carved into the rugged cliffs of Basilicata. Here, ancient cave dwellings known as "sassi" cling to the rocky slopes, offering a glimpse into Italy's distant past. Wander through labyrinthine streets where time seems to stand still, and discover the rich history and cultural heritage of this UNESCO World Heritage Site.
Orvieto
Continuing our exploration, we arrive in Orvieto, a charming hilltop town perched high above the rolling hills of Umbria. Here, Gothic cathedrals and medieval palaces overlook the verdant countryside, creating a scene straight out of a postcard. Explore the town's underground tunnels and ancient Etruscan tombs, and savor the flavors of Umbrian cuisine at a local trattoria.
Polignano a Mare
Our journey then takes us to Polignano a Mare, a hidden gem nestled along the rugged coastline of Puglia. Here, whitewashed buildings cling to the cliffs above crystal-clear waters, creating a breathtaking backdrop for exploration. Stroll along the town's scenic promenade, where panoramic sea views and charming cafes await around every corner.
Alberobello
Next, we discover Alberobello, a UNESCO World Heritage Site renowned for its unique trulli houses. These whitewashed dwellings with conical roofs dot the landscape, creating a scene straight out of a fairytale. Explore the town's winding streets and discover the rich history and traditions of this enchanting corner of Puglia.
San Gimignano
Our journey continues to San Gimignano, a medieval town nestled in the heart of the Tuscan countryside. Here, ancient stone towers pierce the sky, offering panoramic views of the surrounding vineyards and olive groves. Explore the town's well-preserved historic center and savor the flavors of Tuscan cuisine at a local osteria.
Ravello
Next, we venture to Ravello, a hidden gem perched high above the Amalfi Coast in Campania. Here, lush gardens and elegant villas overlook the azure waters of the Mediterranean, creating a scene of unparalleled beauty. Explore the town's historic center and discover the rich artistic heritage that has drawn visitors to this enchanting corner of Italy for centuries.
Urbino
Our final destination is Urbino, a Renaissance town nestled in the hills of Marche. Here, cobblestone streets wind their way through historic palaces and charming piazzas, offering a glimpse into Italy's cultural past. Explore the town's well-preserved architecture and discover the rich artistic heritage that has earned Urbino recognition as a UNESCO World Heritage Site.
Reflect on the Beauty
As our journey comes to a close, we reflect on the beauty and diversity of Italy's hidden gems and charming towns. From the sun-drenched hills of Tuscany to the rugged coastline of Puglia, each destination offers a unique glimpse into Italy's rich cultural tapestry. So why not stray from the beaten path and discover the secrets of these off-the-beaten-path treasures for yourself?
Day trips
Embark on a journey through three captivating Italian cities. Each offering a unique blend of history, culture and culinary delights. From the medieval charm of Siena to the coastal vibrancy of Bari and the artistic allure of Perugia, these day trips promise unforgettable experiences amid Italy's rich tapestry of sights and flavors.
Siena, Italy:
Nestled in the heart of Tuscany, Siena exudes medieval charm with its winding cobblestone streets and Gothic architecture. Start your day trip by exploring the iconic Piazza del Campo, home to the Palio horse race. Wander through the historic city center to marvel at the stunning Siena Cathedral and visit the Museo dell'Opera del Duomo. Don't miss the chance to climb the Torre del Mangia for panoramic views of the city and surrounding countryside. End your day with a leisurely stroll along the city walls, soaking in the timeless beauty of this UNESCO World Heritage Site.
Bari, Italy:
Situated on the Adriatic coast, Bari is a vibrant port city rich in history and culture. Begin your day trip by exploring the historic center, known as Bari Vecchia, where narrow alleys lead to charming piazzas and ancient churches. Visit the Basilica di San Nicola to pay homage to the city's patron saint and marvel at its stunning Romanesque architecture. Don't miss the chance to wander through the bustling fish market and sample local specialties like orecchiette pasta and fresh seafood. End your day with a leisurely stroll along the seafront promenade, where you can soak in the salty sea air and watch the sunset over the Adriatic.
Perugia, Italy:
Perugia, the capital of the Umbria region, is a picturesque hilltop city known for its rich history and artistic heritage. Begin your day trip by exploring the historic city center, where medieval streets wind their way past ancient palaces and churches. Visit the Palazzo dei Priori to admire its stunning Renaissance architecture and explore the Galleria Nazionale dell'Umbria to see works by Perugino and other local artists. Don't miss the chance to stroll along the city's ancient Etruscan walls and take in panoramic views of the surrounding countryside. End your day with a visit to one of Perugia's charming cafes or trattorias, where you can sample traditional Umbrian cuisine and savor a glass of local wine.
Places to eat & drink in Italy
Montepulciano, Tuscany (Breakfast):
Start your day at Caffè Poliziano, a cozy café nestled in the heart of Montepulciano's historic center. Sip on freshly brewed espresso and savor a traditional Italian breakfast of cornetto pastries filled with jam or Nutella. Enjoy views of the town's bustling streets as you indulge in a leisurely morning meal, soaking in the laid-back atmosphere and friendly hospitality.
Matera, Basilicata (Lunch):
For a taste of local cuisine, head to Osteria Pico, a charming trattoria located in the heart of Matera's Sassi district. Feast on hearty dishes like orecchiette pasta with broccoli rabe and spicy sausage, or grilled lamb chops with roasted potatoes. Pair your meal with a glass of Aglianico wine from the nearby vineyards, and savor the flavors of southern Italy in this rustic yet inviting setting.
Orvieto, Umbria (Dinner):
For a memorable dining experience, dine at Trattoria del Moro Aronne, a family-run restaurant housed in a historic building overlooking Orvieto's medieval streets. Feast on traditional Umbrian specialties such as wild boar stew, truffle pasta and roasted pigeon, all made with locally sourced ingredients. Pair your meal with a glass of Orvieto Classico wine, and enjoy the warm ambiance and attentive service that make this trattoria a favorite among locals and visitors alike.
Polignano a Mare, Puglia (Breakfast):
Start your day at Bar Turismo, a charming café located in the heart of Polignano a Mare's old town. Treat yourself to a classic Italian breakfast of cappuccino and cornetto pastries, served with a side of stunning sea views. Situated just steps away from the town's picturesque beach, Bar Turismo is the perfect spot to enjoy a leisurely breakfast while soaking in the beauty of the Adriatic coast.
Alberobello, Puglia (Lunch):
For a taste of authentic Apulian cuisine, head to Trattoria Terra Madre, a family-owned restaurant nestled in the heart of Alberobello's historic district. Feast on homemade pasta dishes like orecchiette with tomato and ricotta sauce, or grilled octopus with potatoes and olives. Pair your meal with a glass of Primitivo wine from the nearby vineyards, and savor the flavors of Puglia in this cozy and welcoming trattoria.
San Gimignano, Tuscany (Dinner):
Indulge in Tuscan cuisine at Cum Quibus, a charming restaurant located in the heart of San Gimignano's historic center. Feast on dishes like ribollita soup, bistecca alla fiorentina and pappa al pomodoro, all made with locally sourced ingredients. Pair your meal with a glass of Chianti Classico wine from the surrounding vineyards, and enjoy the warm ambiance and panoramic views that make Cum Quibus a favorite among locals and visitors alike.
Ravello, Campania (Breakfast):
Start your day at Café Calce, a quaint café located in the heart of Ravello's historic center. Enjoy a leisurely breakfast of freshly baked pastries, homemade yogurt with local honey and freshly squeezed orange juice. Situated just steps away from Ravello's main square, Café Calce offers a peaceful setting to start your day while soaking in the town's charming atmosphere.
Urbino, Marche (Lunch):
For a taste of regional Marche cuisine, head to Osteria del Gufo, a cozy tavern located in the heart of Urbino's historic center. Feast on dishes like tagliatelle al tartufo, porchetta with roasted potatoes and stuffed olives, all made with locally sourced ingredients. Pair your meal with a glass of Verdicchio wine from the nearby vineyards, and enjoy the warm hospitality and rustic charm that make Osteria del Gufo a favorite among locals and visitors alike.
Need to know
Here are a few transportation tips and perspective on locations to the nearest larger towns.
Montepulciano, Tuscany:
Nearest large town: Siena
Best way to travel: The best way to reach Montepulciano is by car, as it allows for flexibility and access to surrounding areas. Alternatively, busses run from Siena to Montepulciano, providing a convenient option for travelers without a car.
Matera, Basilicata:
Nearest large town: Bari
Best way to travel: Matera is best accessed by train or car. Trains run regularly from Bari to Matera, with a journey time of around one hour. Driving offers flexibility and allows for exploration of the surrounding countryside.
Orvieto, Umbria:
Nearest large town: Perugia
Best way to travel: Orvieto is well-connected by train, with regular services running from Perugia and other major cities in Umbria. Traveling by train offers convenience and scenic views of the Umbrian countryside.
Polignano a Mare, Puglia:
Nearest large town: Bari
Best way to travel: The most convenient way to reach Polignano a Mare is by train from Bari, with a journey time of around 30 minutes. Alternatively, driving offers flexibility and allows for exploration of the stunning coastline.
Alberobello, Puglia:
Nearest large town: Bari
Best way to travel: Alberobello can be reached by train from Bari, with a journey time of around one hour. Driving also offers flexibility and allows for exploration of the surrounding countryside and other nearby towns.
San Gimignano, Tuscany:
Nearest large town: Florence
Best way to travel: The best way to reach San Gimignano is by car, as it allows for flexibility and access to surrounding areas. Alternatively, busses run from Florence to San Gimignano, providing a convenient option for travelers without a car.
Ravello, Campania:
Nearest large town: Salerno
Best way to travel: Ravello can be reached by bus from Salerno, with a journey time of around one hour. Driving also offers flexibility and allows for exploration of the stunning Amalfi Coast.
Urbino, Marche:
Nearest large town: Ancona
Best way to travel: Urbino is best accessed by car, as it allows for flexibility and access to surrounding areas. Alternatively, busses run from Ancona to Urbino, providing a convenient option for travelers without a car.
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This guide is part of our ongoing series on travel to Italy and Off-the-Beaten-Path Travel. Looking for more travel inspiration? Check out my guide, Oregon Escapes: 12 Unforgettable Places to Go on Your Next Adventure.